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If you liked Kino no Tabi: The Beautiful World add

...then you might like Jinrui wa Suitai Shimashita add

Jintai and Kino are two radically different takes on a similar subject matter. Kino is a melancholy reflection on society's faults that ultimately portrays them as something to be embraced. Jintai is a vibrant surreal comedy that gleefully lampoons humanity's follies with no hint of sympathy. Consider them two sides of the same coin.

If you liked Hoshi no Koe add

...then you might like Hotarubi no Mori e add

Two people love each other but can't fully express it to due the surrounding circumstances. I'd recommend all of Shinkai's work if you like Hotarubi, not just this one, since they all have a similar theme.

If you liked Kaleido Star add

...then you might like Top wo Nerae! Gunbuster! add

Nothing alike story-wise, but these girls get shit done through hard work and guts! You may also see similarities between the Sora/Layla and Noriko/Kazumi dynamics.

If you liked Ichigo Mashimaro add

...then you might like Yuru Yuri add

Obviously they're both about a group of cute girls, but the style of comedy is also similar. Much of the humor comes from the goofy troublemaker/jokester of the group, Kyouko/Miu. The two characters are pretty similar and pretty much drive their respective shows.

If you liked Haibane Renmei add

...then you might like Saraiya Goyou add

Mellow, slow paced stories about finding solace in another person. They take a character who seems to be on top of it all and slowly reveal that they're not as tough as they initially appear through flashbacks and character development. They come out of their shells and finally find the comfort they've been searching for in the protagonists.

If you liked Shoujo Kakumei Utena add

...then you might like Princess Tutu add

Postmodernist fairy tales, basically.

If you liked K-On!! add

...then you might like The iDOLM@STER add

Cute girls doing cute things with a vague musical theme. However, both get surprisingly emotional towards the end. They both deal with the growing bonds between the girls, and the melancholy feelings that arise as they begin to drift apart, and the threat of separation looms overhead. They both also have well-animated concert scenes, so if you like j-pop and sakuga, at least watch those.

If you liked Neon Genesis Evangelion add

...then you might like Shoujo Kakumei Utena add

Bizarre psychoanalyses of a bunch of fucked up kids. The plots both involve conspiracies of a higher power that those below them aren't aware of, there's also Freudian symbolism everywhere. Basically, Utena is Eva for girls.

If you liked Tsumiki no Ie add

...then you might like Rain Town add

Sad shorts with no dialogue that choose rather to tell their story through beautiful art and music.

If you liked Yokohama Kaidashi Kikou add

...then you might like Otoyomegatari add

Excellent slice of life stories where the beautiful artwork plays a big part in the delivery of the story.

If you liked Koi Kaze add

...then you might like Hourou Musuko add

Both provide a very serious and poignant look at controversial topics that are almost always played as fetishes in anime (crossdressing/gender identity in Hourou Musuko, incest in Koi Kaze).

If you liked Haibane Renmei add

...then you might like So Ra No Wo To add

Gentle slice of lifes that get dramatic towards the end. Both excel in atmosphere and world building. They also both have great soundtracks. Sora no Woto isn't quite as "deep" as Haibane Renmei, character-wise or theme-wise, but it's still got plenty of merit of its own.